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Showing NP-Card for o-Tyrosine (NP0001391)

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Record Information
Version2.0
Created at2007-04-12 21:16:46 UTC
Updated at2021-06-30 02:06:15 UTC
NP-MRD IDNP0001391
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-Tyrosine
DescriptionO-Tyrosine is a normal human metabolite. Its presence is possible due to the hydroxylation of l-phenylalanine by hydroxyl radical (*OH), and is proposed as an hydroxy radical biomarker of oxidative damage to proteins. O-Tyrosine might also be included in the diet and absorbed. It has been associated with disease such as Kwashiorkor, a severe form of protein-energy malnutrition. However, many publications mention that the results are inconclusive, and o-tyrosine is not selectively altered by antioxidant intervention, exercise training or age. (PMID:14670743 , 10969271 , 9887186 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001391 (o-Tyrosine)


  Mrv1652305271900242D          

 13 13  0  0  0  0            999 V2000
   16.1043   -5.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9621   -3.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -3.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9621   -5.0820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -5.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8187   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -3.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8187   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
Download

3D MOL for NP0001391 (o-Tyrosine)

HMDB0006050
     RDKit          3D
o-Tyrosine
 24 24  0  0  0  0  0  0  0  0999 V2000
    2.8607   -1.6273   -0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.6328   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5438   -1.2589    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -0.4489    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -0.5740   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.1588   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    1.1026   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965    1.2602    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437    0.4935    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1004    0.7133    2.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    0.5941    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2327    0.5777    0.8697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.8006   -0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646   -2.4929   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628   -1.8588    0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179   -0.4652   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433   -1.6520    1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677   -2.1950   -0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.3156   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4660    0.0556   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    1.7153   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    2.0052    1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023    1.4026    2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0289    2.6419   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  9  4  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

3D SDF for NP0001391 (o-Tyrosine)


  Mrv1652305271900242D          

 13 13  0  0  0  0            999 V2000
   16.1043   -5.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9621   -3.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -3.4320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9621   -5.0820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -5.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -5.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8187   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -3.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8187   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2477   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)

> <INCHI_KEY>
WRFPVMFCRNYQNR-UHFFFAOYSA-N

> <FORMULA>
C9H11NO3

> <MOLECULAR_WEIGHT>
181.1885

> <EXACT_MASS>
181.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.761927292784808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(2-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-2.34

> <JCHEM_LOGP>
-1.4883343211860007

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.560946219391283

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0057737104028144

> <JCHEM_PKA_STRONGEST_BASIC>
8.880857476560996

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
47.097200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-tyrosine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001391 (o-Tyrosine)

HMDB0006050
     RDKit          3D
o-Tyrosine
 24 24  0  0  0  0  0  0  0  0999 V2000
    2.8607   -1.6273   -0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.6328   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5438   -1.2589    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -0.4489    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -0.5740   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.1588   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    1.1026   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965    1.2602    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437    0.4935    1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1004    0.7133    2.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    0.5941    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2327    0.5777    0.8697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    1.8006   -0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6646   -2.4929   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628   -1.8588    0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179   -0.4652   -1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433   -1.6520    1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677   -2.1950   -0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.3156   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4660    0.0556   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    1.7153   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149    2.0052    1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023    1.4026    2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0289    2.6419   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  9  4  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

PDB for NP0001391 (o-Tyrosine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      30.061 -11.026   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.396  -6.406   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.729  -6.406   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      35.396  -9.486   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      32.729  -9.486   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.062  -8.716   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.729 -11.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.395 -11.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.062 -11.796   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.062  -7.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.395 -13.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.062 -13.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.729 -14.106   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    6                                                            
CONECT    5    6    7                                                       
CONECT    6    4    5   10                                                  
CONECT    7    5    8    9                                                  
CONECT    8    1    7   11                                                  
CONECT    9    7   12                                                       
CONECT   10    2    3    6                                                  
CONECT   11    8   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0001391 (o-Tyrosine)

COMPND    HMDB0006050
HETATM    1  N1  UNL     1       2.861  -1.627  -0.351  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.773  -0.633  -0.513  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.544  -1.259   0.054  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.677  -0.449   0.031  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.603  -0.574  -0.985  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.739   0.159  -1.090  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.006   1.103  -0.117  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.097   1.260   0.929  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.944   0.494   1.005  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.100   0.713   2.079  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.246   0.594   0.112  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.233   0.578   0.870  1.00  0.00           O  
HETATM   13  O3  UNL     1       1.620   1.801  -0.118  1.00  0.00           O  
HETATM   14  H1  UNL     1       2.665  -2.493  -0.880  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.863  -1.859   0.681  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.618  -0.465  -1.629  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.743  -1.652   1.075  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.368  -2.195  -0.559  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.405  -1.316  -1.767  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.466   0.056  -1.895  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.908   1.715  -0.161  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.315   2.005   1.691  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.302   1.403   2.784  1.00  0.00           H  
HETATM   24  H11 UNL     1       2.029   2.642  -0.445  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3   11   16
CONECT    3    4   17   18
CONECT    4    5    5    9
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8   21
CONECT    8    9    9   22
CONECT    9   10
CONECT   10   23
CONECT   11   12   12   13
CONECT   13   24
END
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SMILES for NP0001391 (o-Tyrosine)

NC(CC1=CC=CC=C1O)C(O)=O
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INCHI for NP0001391 (o-Tyrosine)

InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
2-Amino-3-(2-hydroxyphenyl)propanoic acidChEBI
2-Amino-3-(2-hydroxyphenyl)propanoateGenerator
2-Hydroxy-DL-phenylalanineHMDB
2-Hydroxy-phenylalanineHMDB
2-HydroxyphenylalanineHMDB
2-TyrosineHMDB
3-(O-Hydroxyphenyl)DL-alanineHMDB
DL- O-TyrosineHMDB
DL-3-(O-Hydroxyphenyl)alanineHMDB
DL-O-TyrosineHMDB
Ortho-tyrosineHMDB
2-Tyrosine, (D)-isomerHMDB
2-Tyrosine, (DL)-isomerHMDB
2-Tyrosine, (L)-isomerHMDB
Chemical FormulaC9H11NO3
Average Mass181.1885 Da
Monoisotopic Mass181.07389 Da
IUPAC Name2-amino-3-(2-hydroxyphenyl)propanoic acid
Traditional Name2-tyrosine
CAS Registry Number2370-61-8
SMILES
NC(CC1=CC=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C9H11NO3/c10-7(9(12)13)5-6-3-1-2-4-8(6)11/h1-4,7,11H,5,10H2,(H,12,13)
InChI KeyWRFPVMFCRNYQNR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-05View Spectrum
Species
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Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.57 g/LALOGPS
logP-2.3ALOGPS
logP-1.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability17.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006050
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023822
KNApSAcK IDNot Available
Chemspider ID82607
KEGG Compound IDNot Available
BioCyc IDCPD0-923
BiGG IDNot Available
Wikipedia LinkTyrosine
METLIN IDNot Available
PubChem Compound91482
PDB IDNot Available
ChEBI ID91038
Good Scents IDNot Available
References
General References
  1. Orhan H, Vermeulen NP, Tump C, Zappey H, Meerman JH: Simultaneous determination of tyrosine, phenylalanine and deoxyguanosine oxidation products by liquid chromatography-tandem mass spectrometry as non-invasive biomarkers for oxidative damage. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jan 25;799(2):245-54. [PubMed:14670743 ]
  2. Leeuwenburgh C, Hansen PA, Holloszy JO, Heinecke JW: Oxidized amino acids in the urine of aging rats: potential markers for assessing oxidative stress in vivo. Am J Physiol. 1999 Jan;276(1 Pt 2):R128-35. [PubMed:9887186 ]
  3. Reddy MK, Bhajammanavar V, Baidya M: Annulation Cascade of Sulfamate-Derived Cyclic Imines with Glycine Aldimino Esters: Synthesis of 1,3-Benzoxazepine Scaffolds. Org Lett. 2021 May 21;23(10):3868-3872. doi: 10.1021/acs.orglett.1c01001. Epub 2021 May 6. [PubMed:33956452 ]
  4. Quan H, Zhang Y, Yin P, Zhao L: Effects of two algicidal substances, ortho-tyrosine and urocanic acid, on the growth and physiology of Heterosoigma akashiwo. Environ Pollut. 2021 Sep 1;284:117004. doi: 10.1016/j.envpol.2021.117004. Epub 2021 Mar 23. [PubMed:33906037 ]
  5. Pelclova D, Navratil T, Fenclova Z, Vlckova S: Markers of oxidative stress after three days of nanoTiO2 sunscreen use in humans: a pilot study. Cent Eur J Public Health. 2020 Oct;28 Suppl:S17-S21. doi: 10.21101/cejph.a6158. [PubMed:33069176 ]